at risk of getting eaten, I'd like to put in a non-type post...
it sounds like he's getting hurt, and he feels threatened and not safe to let down the barriers and relax.
his ambitions in life and his "things to do before 30" are probably important to him, not necessarily because he wants to aspire to some daft pointless and stupid shallow ideal that has been programmed into him, but it might be because he is a. aware of his own mortality and limited chance at life (in a realistic way) and b. he's able to enjoy his achievements and self-actualize to some extent (or he is trying to be able to do those things.)
I know what its like to be at a place where psychologically there are unmet needs at the kind of level that make it impossible to even understand getting that kind of thing out of life. It can make some of the actions of people who do look idiotic. (Not to say people don't ever take idiotic actions or have idiotic wants, lol.)
I suppose if you put his list into a more relationship-orientated mindset, it could read something like,
"I need to be accepted"
"I need to feel supported in the things that are important to me"
"I need to be able to feel safe to be emotionally open and relaxed with you"
*waits to be eaten*

The next bit I'm not experienced with handling - I've mostly kept relationships at a distance in some way. (normally literally, lol.)
Its true you do have to question whether you're compatible in the practical sense too regardless how the two of you feel about each other. If one person wants a quiet life close to a reliable person who is always there for them and another wants adventure and travel, you might not be able to give each other what you need. While that doesn't change how you feel, if you both care about each others' needs being met as well as your own its possible to see how you do have to think about whether you would be able to be happy together in any kind of traditional relationship set up, and if that kind of thing is what you want from life, you need to think about what will make you happy in the long term.
If you are thinking about getting together with any person, I guess you need to think about what you would want from life, and a relationship, and how you'd like the two to relate to each other if that makes sense.